TWI738753B - 雜環化合物 - Google Patents
雜環化合物 Download PDFInfo
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- TWI738753B TWI738753B TW106110783A TW106110783A TWI738753B TW I738753 B TWI738753 B TW I738753B TW 106110783 A TW106110783 A TW 106110783A TW 106110783 A TW106110783 A TW 106110783A TW I738753 B TWI738753 B TW I738753B
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Classifications
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
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- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Psychology (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
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| GB201116559D0 (en) | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| JOP20160086B1 (ar) | 2015-05-08 | 2021-08-17 | 2 Katholieke Univ Leuven Ku Leuven Research And Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20160198B1 (ar) | 2015-09-16 | 2022-03-14 | Janssen Pharmaceuticals Inc | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JO3633B1 (ar) | 2015-09-16 | 2020-08-27 | Katholieke Univ Leuven Ku Leuven Research & Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| US10610520B2 (en) | 2016-03-31 | 2020-04-07 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| HUE054936T2 (hu) | 2016-03-31 | 2021-10-28 | Janssen Pharmaceuticals Inc | Helyettesített indol-származékok mint a dengue-vírus replikációjának inhibitorai |
| MX2018011788A (es) | 2016-03-31 | 2019-05-20 | Janssen Pharmaceuticals Inc | Derivados de indolina sustituidos como inhibidores de la replicacion virica de dengue. |
| AU2017240076A1 (en) | 2016-04-01 | 2018-08-09 | Janssen Pharmaceuticals, Inc. | Substituted indole compound derivatives as dengue viral replication inhibitors |
| JOP20170069B1 (ar) | 2016-04-01 | 2021-08-17 | 1 Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| JOP20180025B1 (ar) | 2017-03-31 | 2021-08-17 | Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180026A1 (ar) | 2017-03-31 | 2019-01-30 | Univ Leuven Kath | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| CN110753682B (zh) | 2017-05-22 | 2023-06-30 | 杨森制药公司 | 作为登革热病毒复制抑制剂的经取代的吲哚啉衍生物 |
| ES2929667T3 (es) | 2017-05-22 | 2022-11-30 | Janssen Pharmaceuticals Inc | Derivados de indolina sustituidos como inhibidores de la replicación vírica de dengue |
| AU2018323459A1 (en) | 2017-08-29 | 2020-02-20 | H. Lundbeck A/S. | Spirocycle compounds and methods of making and using same |
| EP3689879B1 (en) | 2017-09-29 | 2025-02-12 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| AR114136A1 (es) | 2017-10-10 | 2020-07-29 | Hoffmann La Roche | Compuestos heterocíclicos |
| EP3717477B1 (en) * | 2017-11-28 | 2022-07-20 | F. Hoffmann-La Roche AG | New heterocyclic compounds |
| TW201930300A (zh) * | 2017-12-15 | 2019-08-01 | 瑞士商赫孚孟拉羅股份公司 | 新雜環化合物 |
| EP3737680A1 (en) | 2018-01-08 | 2020-11-18 | F. Hoffmann-La Roche AG | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| RS65912B1 (sr) | 2018-08-13 | 2024-10-31 | Hoffmann La Roche | Nova heterociklična jedinjenja kao inhibitori monoacilglicerol lipaze |
| BR112020025642A2 (pt) * | 2018-08-13 | 2021-03-23 | F. Hoffmann-La Roche Ag | compostos heterocíclicos como inibidores da monoacilglicerol lipase |
| JP7609854B2 (ja) | 2019-09-12 | 2025-01-07 | エフ. ホフマン-ラ ロシュ アーゲー | Magl阻害剤としての4,4a,5,7,8,8a-ヘキサピリド[4,3-b][1,4]オキサジン-3-オン化合物 |
| JOP20220180A1 (ar) * | 2020-02-10 | 2023-01-30 | Janssen Pharmaceutica Nv | مُعدلات ليباز أُحادِيُّ الجلِيسِريد |
| JP7729831B2 (ja) * | 2020-03-26 | 2025-08-26 | ヤンセン ファーマシューティカ エヌ.ベー. | モノアシルグリセロールリパーゼ調節因子としてのアミノシクロブタン |
| BR112022019155A2 (pt) | 2020-03-26 | 2022-12-06 | Janssen Pharmaceutica Nv | Aril piperidinas como moduladores da monoacilglicerol lipase |
| AU2021241888A1 (en) * | 2020-03-26 | 2022-09-29 | Janssen Pharmaceutica Nv | Azaspirocycles as monoacylglycerol lipase modulators |
| CN115989228A (zh) | 2020-09-03 | 2023-04-18 | 豪夫迈·罗氏有限公司 | 杂环化合物 |
| UY39516A (es) | 2020-11-13 | 2022-05-31 | H Lundbeck As | Composición para el tratamiento de una enfermedad vascular, composición para la prevención de una enfermedad vascular, composición para el tratamiento de la hipertensión, y composición para la prevención de la hipertensión |
| KR20240005747A (ko) | 2021-05-08 | 2024-01-12 | 얀센 파마슈티카 엔브이 | 치환된 스피로 유도체 |
| US11974987B2 (en) | 2021-08-09 | 2024-05-07 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators for use in autism spectrum disorders |
| WO2023130023A1 (en) | 2021-12-29 | 2023-07-06 | Psy Therapeutics, Inc. | Inhibiting monoacylglycerol lipase (magl) |
| CN115925699B (zh) * | 2022-02-25 | 2023-10-03 | 南京知和医药科技有限公司 | 具有镇痛活性的稠环化合物及其制备方法与用途 |
| CN119137114A (zh) | 2022-05-04 | 2024-12-13 | H.隆德贝克有限公司 | 作为单酰基甘油脂肪酶抑制剂的(s)-1-(哒嗪-3-基氨基甲酰基)-6-氮杂螺[2.5]辛烷-6-甲酸1,1,1,3,3,3-六氟丙-2-酯的结晶形式 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012054716A1 (en) * | 2010-10-22 | 2012-04-26 | Janssen Pharmaceutica Nv. | Piperidin-4-yl-azetidine diamides as monoacylglycerol lipase inhibitors |
| WO2015106058A1 (en) * | 2014-01-09 | 2015-07-16 | Merck Patent Gmbh | Pyrimidine pyrazolyl derivatives and their use as irak inhibitors |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE469875T1 (de) * | 2002-03-13 | 2010-06-15 | Schering Corp | Nk1-antagonisten |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| TWI495637B (zh) | 2009-04-22 | 2015-08-11 | Janssen Pharmaceutica Nv | 用作單醯基甘油脂肪酶抑制劑之雜芳族及芳族六氫吡基吖丁啶基醯胺(一) |
| KR20120005517A (ko) | 2009-04-22 | 2012-01-16 | 얀센 파마슈티카 엔.브이. | 모노아실글리세롤 리파제 억제제로서의 헤테로방향족 및 방향족 피페라지닐 아제티디닐 아미드 |
| US8415341B2 (en) | 2009-04-22 | 2013-04-09 | Janssen Pharmaceutica, Nv | Heteroaromatic and aromatic piperazinyl azetidinyl amides as monoacylglycerol lipase inhibitors |
| AR076381A1 (es) | 2009-04-22 | 2011-06-08 | Janssen Pharmaceutica Nv | Azetidinil diamidas como inhibidores de monoacilglicerol lipasa |
| EP2486034A1 (en) * | 2009-10-07 | 2012-08-15 | Bristol-Myers Squibb Company | Spirocyclic compounds as modulators of chemokine receptor activity |
| WO2012030907A1 (en) | 2010-09-03 | 2012-03-08 | Janssen Pharmaceutica Nv | Di-azetidinyl diamide as monoacylglycerol lipase inhibitors |
| KR20140001206A (ko) | 2010-09-27 | 2014-01-06 | 얀센 파마슈티카 엔.브이. | 모노아실글리세롤 리파아제 억제제로서의 옥소피페라진-아제티딘 아미드 및 옥소다이아제핀-아제티딘 아미드 |
| US8513423B2 (en) | 2010-10-22 | 2013-08-20 | Janssen Pharmaceutica, Nv | Piperidin-4-yl-azetidine diamides as monoacylglycerol lipase inhibitors |
| CN103957916A (zh) | 2011-09-30 | 2014-07-30 | 詹森药业有限公司 | 用于治疗代谢疾病和相关失调的单酰甘油脂肪酶抑制剂 |
| MX2014003883A (es) | 2011-09-30 | 2014-08-27 | Janssen Pharmaceutica Nv | Inhibidores de monoacilglicerol lipasa para el tratamiento de enfermedades metabolicas y transtornos relacionados. |
| EA028085B1 (ru) * | 2012-01-06 | 2017-10-31 | Эбайд Терапьютикс, Инк. | Карбаматные соединения и их применение |
| EP3087067B1 (en) | 2013-12-26 | 2018-10-24 | Takeda Pharmaceutical Company Limited | 4-(piperrazin-1-yl)-pyrrolidin-2-one compounds as monoacylglycerol lipase (magl) inhibitors |
| WO2016158956A1 (ja) | 2015-03-30 | 2016-10-06 | 武田薬品工業株式会社 | 複素環化合物 |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012054716A1 (en) * | 2010-10-22 | 2012-04-26 | Janssen Pharmaceutica Nv. | Piperidin-4-yl-azetidine diamides as monoacylglycerol lipase inhibitors |
| WO2015106058A1 (en) * | 2014-01-09 | 2015-07-16 | Merck Patent Gmbh | Pyrimidine pyrazolyl derivatives and their use as irak inhibitors |
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